voriconazole
Trade name: vfend
Approved
May 24, 2002
Voriconazole (vor-i-KON-a-zole, brand name Vfend, Pfizer) is a triazole antifungal medication. VFEND® (voriconazole) is available as film-coated tablets for oral administration, and as a lyophilized powder for solution for intravenous infusion. Voriconazole is a triazole antifungal agent indicated for use in the treatment of fungal infections including invasive aspergillosis, esophageal candidiasis, and serious fungal infections caused by Scedosporium apiospermum (asexual form of Pseudallescheria boydii) and Fusarium spp. including Fusarium solani. Fungal plasma membranes are similar to mammalian plasma membranes, differing in having the nonpolar sterol ergosterol, rather than cholesterol, as the principal sterol. Membrane sterols such as ergosterol provide structure, modulation of membrane fluidity, and possibly control of some physiologic events. Voriconazole effects the formation of the fungal plasma membrane by indirectly inhibiting the biosynthesis of ergosterol. This results in plasma membrane permeability changes and inhibition of growth. The primary mode of action of voriconazole is the inhibition of fungal cytochrome P-450-mediated 14 alpha-lanosterol demethylation, an essential step in fungal ergosterol biosynthesis. The accumulation of 14 alpha-methyl sterols correlates with the subsequent loss of ergosterol in the fungal cell wall and may be responsible for the antifungal activity of voriconazole. Voriconazole has been shown to be more selective for fungal cytochrome P-450 enzymes than for various mammalian cytochrome P-450 enzyme systems. The most common side effects associated with voriconazole include transient visual disturbances, fever, rash, vomiting, nausea, diarrhea, headache, sepsis, peripheral edema, abdominal pain, and respiratory disorder. Unlike most adverse effects, which are similar to other azole antifungal agents, visual disturbances (such as blurred vision or increased sensitivity to light) are unique to voriconazole. Though rare, there have been cases of serious hepatic reactions during treatment with voriconazole (a class effect of azole antifungal agents). Liver function tests should be evaluated at the start of and during the course of therapy. Voriconazole is phototoxic. It has been associated with an increased risk of squamous-cell carcinoma of the skin — NCATS
Clinical trial activity
123 trials · 129 clinical orgs · 34 marketing orgs
Earliest trial started Jun 1, 1997 (NCT00003031)
Timeline
1990s
2000s
2010s
- Apr 22, 2010
Mylan — Marketing Organization
- Dec 12, 2011
Sandoz — Marketing Organization
- Dec 12, 2011
Novartis — Marketing Organization
- Apr 6, 2012
Teva — Marketing Organization
- Sep 2, 2015
Glenmark Pharmaceuticals — Marketing Organization
- Jan 22, 2016
Aurobindo Pharma — Marketing Organization
- Mar 23, 2016
Alvogen — Marketing Organization
- Mar 23, 2016
Almaject — Marketing Organization
- Apr 13, 2016
Amneal Pharmaceuticals — Marketing Organization
- May 24, 2016
Ajanta Pharma Ltd — Marketing Organization
- May 24, 2016
Appco Pharma — Marketing Organization
- May 24, 2016
Novel Anti-Infective Technologies, LLC — Marketing Organization
- May 24, 2016
Zydus Discovery DMCC — Marketing Organization
- May 24, 2016
Cadila Healthcare — Marketing Organization
- May 24, 2016
Rising Pharmaceuticals — Marketing Organization
- May 24, 2016
Chartwell Pharmaceuticals — Marketing Organization
- Aug 8, 2016
Prinston Inc — Marketing Organization
- Sep 7, 2016
Akorn, Inc. — Marketing Organization
- Sep 7, 2016
Epic Pharma Llc — Marketing Organization
- Mar 9, 2017
Xellia Pharmaceuticals — NDA Secondary Org
- Mar 9, 2017
Novo Nordisk — NDA Secondary Org
- Mar 9, 2017
Hikma — Marketing Organization
- Nov 30, 2018
Hainan Poly Pharm — Marketing Organization
- Nov 30, 2018
SLATE RUN PHARMA — Marketing Organization
2020s
- Mar 31, 2020
Gland Pharma Ltd — Marketing Organization
- Mar 31, 2020
Fosun — Marketing Organization
- May 9, 2022
Meitheal — Marketing Organization
- Oct 11, 2022
PHARMOBEDIENT — Marketing Organization
- Feb 2, 2023
Eugia Pharma — Marketing Organization
- Mar 9, 2023
UBI Pharma Inc. — Marketing Organization
- Jan 2, 2024
ZHEJIANG POLY PHARM — Marketing Organization
- Apr 3, 2024
Aspiro — Marketing Organization
- Aug 8, 2025
Hetero Labs Ltd — Marketing Organization
Indications
Approved for
Studied for
- Acquired Immunodeficiency Syndrome · Phase 3
- Anesthesia · Phase 1
- Aspergillosis, Allergic Bronchopulmonary · Phase 2/Phase 3
- Asthma · Phase 1
- Bacterial Infections · Phase 1
- Biological Availability · Phase 4
- Blastomycosis · Phase 4
- Burns · Phase 1
- Candidemia · Phase 4
- Candidiasis · Phase 4
- Candidiasis, Invasive · Phase 4
- Corneal Ulcer · Phase 3
- Critical Illness · Phase 4
- Cryptococcosis · Phase 4
- Cystic Fibrosis · Phase 2
- Dermatomycoses · Phase 2
- Drug Interactions · Phase 4
- Drug Resistance, Microbial · Early Phase 1
- Eye Infections, Fungal · Phase 3
- Fungemia · Phase 3
- Fusarium · Phase 2
- Graft vs Host Disease · Phase 1
- Healthy Volunteers · Phase 4
- Hematologic Neoplasms · Phase 4
- Hematopoietic Stem Cell Transplantation · Phase 2
- HIV Infections · Phase 3
- Hyperalgesia · Phase 1
- Hyperthermia · Phase 1
- Immunocompromised Host · Phase 2
- Immunologic Deficiency Syndromes · Phase 3
- Invasive Fungal Infections · Phase 4
- Invasive Pulmonary Aspergillosis · Phase 4
- Keratitis · Phase 3
- Kidney Neoplasms · Phase 2
- Kidney Transplantation · Phase 4
- Leishmaniasis, Cutaneous · Phase 3
- Leukemia · Phase 3
- Leukemia, B-Cell · Phase 1
- Leukemia, Lymphocytic, Chronic, B-Cell · Phase 1
- Leukemia, Myeloid, Acute · Phase 3
- Leukemia, Myelomonocytic, Chronic · Phase 1/Phase 2
- Lung Diseases · Phase 3
- Lymphoma · Phase 3
- Meningitis, Cryptococcal · Early Phase 1
- Multiple Myeloma · Phase 2
- Mycoses · Phase 4
- Mycosis Fungoides · Phase 4
- Myelodysplastic Syndromes · Phase 2
- Myeloproliferative Disorders · Phase 2
- Neoplasms · Phase 2
- Neuroaspergillosis · Phase 3
- Neuroblastoma · Phase 2
- Neutropenia · Phase 3
- Pain · Phase 1
- Pharmacokinetics · Phase 2
- Photothermal Therapy · Early Phase 1
- Precursor B-Cell Lymphoblastic Leukemia-Lymphoma · Phase 1/Phase 2
- Procedural Sedation · Phase 1
- Pulmonary Disease, Chronic Obstructive · Phase 4
- Renal Insufficiency · Phase 1/Phase 2
- Sarcoma · Phase 2
- Stem Cell Transplantation · Phase 1
- Tinea Versicolor · Phase 2
- Voriconazole · Phase 4
Mechanism of action
- Cytochrome P450 51INHIBITOR
ERG11 inhibitor
Approval history
- approvedMay 24, 2002
Chemistry & pharmacology
SMILES
C[C@@H](C1=NC=NC=C1F)[C@](O)(CN2C=NC=N2)C3=CC=C(F)C=C3F- Mol. weight
- 349.3105 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Prescription Only
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- WikipediaVoriconazole ↗
- NCATSJFU09I87TR ↗
- ChEMBLCHEMBL638 ↗
Also known as
- (r-(r*,s*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
- (r-(r*,s*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1h-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
- uk109496
- uk 109496
- uk-109496
- uk-109496
- uk-109496
- vcz
- vcz
- vfend
- vfend
- vfend
- vfend
- voriconazol
- voriconazol
- voriconazol
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazole
- voriconazolum
- voriconazolum
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06680544 | Phase 2 | Nov 15, 2024 | Sheikh Zayed Medical College |
| NCT06582186 | Phase 4 | Oct 31, 2024 | University of Grenoble |
| NCT06493409 | Phase 1 | Aug 26, 2024 | Bristol-Myers Squibb |
| NCT05458102 | Phase 1 | Aug 19, 2022 | Gilead Sciences |
| NCT05264142 | Phase 1 | Apr 1, 2022 | University of Geneva |
| NCT05708625 | Phase 3 | Jan 1, 2022 | Zagazig University |
| NCT05268718 | Early Phase 1 (Phase 1) | Aug 1, 2021 | Zhejiang University |
| NCT04865419 | Phase 1/Phase 2 (Phase 2) | Jun 11, 2021 | AstraZeneca, University of Texas at Houston |
| NCT04876716 | Phase 3 | May 11, 2021 | Erasmus University Rotterdam, HOVON - Dutch Haemato-Oncology Association, ZonMw: The Netherlands Organisation for Health Research and Development |
| NCT04752163 | Phase 1/Phase 2 (Phase 2) | Mar 25, 2021 | University of Texas at Houston |
| NCT04824417 | Phase 3 | Mar 1, 2021 | Postgraduate Institute of Medical Education and Research |
| NCT04551963 | Phase 1 | Nov 15, 2020 | BeOne Medicines |
| NCT04576325 | Phase 1 | Nov 2, 2020 | TFF Pharmaceuticals, TFF Pharmaceuticals, Inc. |
| NCT04552353 | Phase 4 | Jun 13, 2020 | Yung Shin Pharm. Ind. Co., Ltd. |
| NCT05330000 | Phase 1 | May 22, 2020 | Qingdao University |
| NCT04229303 | Phase 1 | Feb 29, 2020 | Zambon |
| NCT04238884 | Phase 4 | Jan 2, 2020 | Universidad Autonoma de Madrid |
| NCT04072640 | Early Phase 1 (Phase 1) | Jan 1, 2020 | Wenzhou Medical University, Zhejiang University |
| NCT04872231 | Phase 1 | Nov 22, 2019 | TFF Pharmaceuticals, TFF Pharmaceuticals, Inc. |
| NCT04145583 | Phase 1 | Nov 15, 2019 | Haisco Pharmaceutical, Soochow University |
Organizations
Research & Development (129)
Marketing (41)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Ajanta Pharma Ltd | For profit | MKTG | May 24, 2016 |
| Akorn, Inc. | For profit | MKTG | Sep 7, 2016 |
| Almaject | For profit | MKTG | Mar 23, 2016 |
| Alvogen | For profit | MKTG | Mar 23, 2016 |
| Alvogen | For profit | SYN | Mar 23, 2016 |
| Amneal Pharmaceuticals | For profit | MKTG | Apr 13, 2016 |
| Appco Pharma | For profit | MKTG | May 24, 2016 |
| Appco Pharma | For profit | SYN | May 24, 2016 |
| Aspiro | For profit | MKTG | Apr 3, 2024 |
| Aurobindo Pharma | For profit | MKTG | Jan 22, 2016 |
| Cadila Healthcare | For profit | MKTG | May 24, 2016 |
| Chartwell Pharmaceuticals | For profit | MKTG | May 24, 2016 |
| Epic Pharma Llc | For profit | MKTG | Sep 7, 2016 |
| Eugia Pharma | For profit | MKTG | Feb 2, 2023 |
| Fosun | For profit | MKTG | Mar 31, 2020 |
| Gland Pharma Ltd | For profit | MKTG | Mar 31, 2020 |
| Gland Pharma Ltd | For profit | SYN | Mar 31, 2020 |
| Glenmark Pharmaceuticals | For profit | MKTG | Sep 2, 2015 |
| Hainan Poly Pharm | For profit | MKTG | Nov 30, 2018 |
| Hainan Poly Pharm | For profit | SYN | Jan 2, 2024 |
| Hetero Labs Ltd | For profit | MKTG | Aug 8, 2025 |
| Hikma | For profit | MKTG | Mar 9, 2017 |
| Meitheal | For profit | MKTG | May 9, 2022 |
| Mylan | For profit | MKTG | Apr 22, 2010 |
| Mylan | For profit | SYN | Oct 11, 2022 |
| Novartis | For profit | MKTG | Dec 12, 2011 |
| Novel Anti-Infective Technologies, LLC | For profit | MKTG | May 24, 2016 |
| Novo Nordisk | For profit | NDA2 | Mar 9, 2017 |
| PHARMOBEDIENT | For profit | MKTG | Oct 11, 2022 |
| Pfizer | For profit | SYN | May 24, 2002 |
| Pfizer | For profit | NDA | May 24, 2002 |
| Pfizer | For profit | IND | Aug 1, 1995 |
| Prinston Inc | For profit | MKTG | Aug 8, 2016 |
| Rising Pharmaceuticals | For profit | MKTG | May 24, 2016 |
| SLATE RUN PHARMA | For profit | MKTG | Nov 30, 2018 |
| Sandoz | For profit | MKTG | Dec 12, 2011 |
| Teva | For profit | MKTG | Apr 6, 2012 |
| UBI Pharma Inc. | For profit | MKTG | Mar 9, 2023 |
| Xellia Pharmaceuticals | For profit | NDA2 | Mar 9, 2017 |
| ZHEJIANG POLY PHARM | For profit | MKTG | Jan 2, 2024 |
| Zydus Discovery DMCC | For profit | MKTG | May 24, 2016 |